This project involves the development of methodologies that provide convenient access to homogeneous glycoproteins. Specifically, the PI and his undergraduate research team at Seattle University (SU) will develop a novel, efficient de novo synthesis of N-linked glycopeptides that employs -glycosylhydrazides, generated via hydrazide glycosylation, as -glycosylamine surrogates. The proposed method to synthesize N-linked glycopeptides will harness hydrazide glycosylation reactions to provide glycopeptides with natural glycosidic linkages and with greater efficiency than traditional methods. Current oxyamine and hydrazide glycosylation methods produce glycoproteins with non-natural N-linked glycoproteins containing oxime, oxyamine, or hydrazine glycan-peptide linkages and thus current methods make it difficult for chemists and biologists to study with confidence the influence of glycan structure on protein function. The PI chose to pursue his independent career at SU, a predominantly undergraduate institution, so that his research program could simultaneously impact the scientific community and transform the lives of undergraduate students. All of the research the PI has performed since he began his career at SU in 2005 has been done in collaboration with undergraduate research students; undergraduate students will work side-by-side with the PI on all aspects of the work proposed here.